Herbicidal o-aryl or alkarylsulfonylureas

ABSTRACT

N-(heterocyclicaminocarbonyl)-o-(aryl or alkaryl)benzenesulfonamides, such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-[1,1&#39;-biphenyl]-2- sulfonamide are useful as preemergent or postemergent herbicides or as plant growth regulants.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. Ser. No. 168,347,filed July 11, 1980, (now abandoned).

BACKGROUND OF THE INVENTION

This invention relates to novelN-(heterocyclicaminocarbonyl)-o-(hydrocarbyl) benzenesulfonamides whichare useful as agricultural chemicals and in particular as herbicides andgrowth regulants.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (I) and their use as general orselective herbicides: ##STR1## wherein R₁ and R₂ may independently bealkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

Compounds of Formula (II), and their use as antidiabetic agents, arereported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.

In U.S. Pat. No. 4,127,405, compounds are disclosed of the generalformula: ##STR3## R₃ and R₆ are independently hydrogen, fluorine,chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atomsor alkoxy of 1-2 carbon atoms;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbonatoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Z is methyl or methoxy; or their agriculturally suitable salts; providedthat:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ isother than hydrogen and at least two of R₃, R₄, R₆ and R₇ must behydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other thanhydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine ormethyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ mustbe hydrogen.

In particular, the patent discloses orthosubstituted compounds whereinthe substitution is C₁ -C₄ alkyl.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodneeds, such as soybeans, corn, wheat and the like. The currentpopulation explosion and concomitant world food shortage demandimprovements in the efficiency of producing these crops. Preventing orminimizing the loss of a portion of such valuable crops by killing, orinhibiting the growth of undesired vegetation is one way of improvingthis efficiency.

A wide variety of materials useful for killing, or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. However, the needexists for still more effective herbicides that destroy or retard weedswithout causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, suitableagricultural compositions containing them, and their method of use asgeneral, as well as, selective herbicides. ##STR4## n is 0 or 1; R₁ isH, F, Cl, Br, NO₂, CF₃, C₁ -C₄ alkyl, OCF₃ or C₁ -C₄ alkoxy;

R₂ and R₃ are selected independently from H and CH₃ ;

R₄ is H, C₁ -C₃ alkyl, F, Cl, Br, CF₃, OCF₃ or C₁ -C₃ alkoxy;

R₅ is CH₃, Cl, Br or H;

A is ##STR5## X is H, CH₃, OCH₃, OCH₂ CH₃, OCH₂ CF₃, CH₂ OCH₃ or Cl;

Y is CH₃, OCH₃ or OCH₂ CH₃ ;

Z is N, CH, CCl, C-Br, C-CN, CCH₃, C-CH₂ CH₃, C-CH₂ CH₂ Cl or C-CH₂CH=CH₂ ;

Y¹ is H, CH₃, OCH₃ or Cl; and

Q is CH₂ or O;

provided that the total number of carbons in R is less than or equal tonine.

PREFERRED COMPOUNDS

Preferred for reasons of higher herbicidal activity and/or morefavorable ease of synthesis are:

(1) Compounds of Formula I in which n is 0;

(2) Compounds of Preferred 1 in which

A is ##STR6## X is CH₃, OCH₃, OCH₂ CH₃ or CH₂ OCH₃ ; Y is CH₃ or OCH₃ ;and

Z is CH or N.

(3) Compounds of Preferred 2 in which R₅ is H, and R₄ is H or Cl.

(4) Compounds of Preferred 3 in which R₁ is H or Cl.

Specifically preferred for highest herbicidal activity and/or mostfavorable ease of synthesis are:

3,2'-dichloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide;

DETAILED DESCRIPTION OF THE INVENTION

The compounds of Formula I can be made by the reaction sequence:##STR7##

Sulfonyl isocyanates can be made, for example, by the method of Ulrichet al., [J. Org. Chem. 34, 3200 (1969)]. The sulfonamide is boiled underreflux with an excess of thionyl chloride, which functions as a reactantand solvent. The reaction is continued until the sulfonamide protons areundetectable in the proton resonance spectrum. An overnight reactionperiod (about 16 hours) is generally sufficient. The thionyl chloride isevaporated and the residue dissolved in an inert solvent (such astoluene, benzene, xylene, etc.), contacted with a catalytic amount ofpyridine, then with at least one equivalent of phosgene. The mixture isheated to about 60°-140°, with 80°-100° preferred. Conversion to theisocyanate is substantially complete within about 1/4 to 3 hours. Themixture containing the sulfonyl isocyanate can be used directly for thenext reaction step (formation of sulfonylurea) or the sulfonylisocyanate can be isolated by filtration and evaporation of the solvent.The isocyanate can be redissolved in a suitable solvent (e.g., methylenechloride, benzene, toluene, xylene or acetonitrile, etc.) and thesolution contacted with the aminoheterocycle H₂ N--A to provide thesulfonylurea product. The reaction is generally exothermic.Conveniently, the starting reaction temperature is ambient, but can bevaried from about 0° to 100° if desired. The product can be isolated byfiltration if it precipitates from the reaction mixture; otherwise, thesolvent can be evaporated and the residual product obtained thereby,with optional further purification obtained by trituration with anorganic solvent (e.g., diethyl ether, 1-chlorobutane, etc.) in which itis only sparingly soluble.

Exemplary compounds of structure I are listed below:

                  TABLE I                                                         ______________________________________                                         ##STR8##                                                                     R.sub.1       R              m.p. °C.                                  ______________________________________                                                       ##STR9##      78° (dec.)                                6-F                                                                                          ##STR10##                                                      6-Cl                                                                                         ##STR11##                                                      6-Br                                                                                         ##STR12##                                                      4-NO.sub.2                                                                                   ##STR13##                                                      6-CF.sub.3                                                                                   ##STR14##                                                      6-CH.sub.3                                                                                   ##STR15##                                                      4-CH.sub.3 (CH.sub.2).sub.3                                                                  ##STR16##                                                      6-CF.sub.3 O                                                                                 ##STR17##                                                      6-CH.sub.3 O                                                                                 ##STR18##                                                      4-CH.sub.3 (CH.sub.2).sub.3 O                                                                ##STR19##                                                      H                                                                                            ##STR20##                                                      H                                                                                            ##STR21##                                                      H                                                                                            ##STR22##                                                      H                                                                                            ##STR23##                                                      H                                                                                            ##STR24##                                                      3-Cl                                                                                         ##STR25##                                                      4-Cl                                                                                         ##STR26##                                                      5-Cl                                                                                         ##STR27##                                                      H                                                                                            ##STR28##                                                      H                                                                                            ##STR29##                                                      H                                                                                            ##STR30##                                                      H                                                                                            ##STR31##                                                      H                                                                                            ##STR32##                                                      H                                                                                            ##STR33##                                                      H                                                                                            ##STR34##                                                      6-CH.sub.3 (CH.sub.2).sub.2 O                                                                ##STR35##                                                      H                                                                                            ##STR36##                                                      H                                                                                            ##STR37##                                                      H                                                                                            ##STR38##                                                      H                                                                                            ##STR39##                                                      H                                                                                            ##STR40##                                                      H                                                                                            ##STR41##                                                      H                                                                                            ##STR42##                                                      H                                                                                            ##STR43##                                                      ______________________________________                                    

                  TABLE II                                                        ______________________________________                                         ##STR44##                                                                    R.sub.1       R              m.p. °C.                                  ______________________________________                                                       ##STR45##     128-130                                          6-F                                                                                          ##STR46##                                                      6-Cl                                                                                         ##STR47##                                                      6-Br                                                                                         ##STR48##                                                      4-NO.sub.2                                                                                   ##STR49##                                                      6-CF.sub.3                                                                                   ##STR50##                                                      6-CH.sub.3                                                                                   ##STR51##                                                      4-CH.sub.3 (CH.sub.2).sub.3                                                                  ##STR52##                                                      6-CF.sub.3 O                                                                                 ##STR53##                                                      6-CH.sub.3 O                                                                                 ##STR54##                                                      4-CH.sub.3 (CH.sub.2).sub.3 O                                                                ##STR55##                                                      H                                                                                            ##STR56##                                                      H                                                                                            ##STR57##                                                      H                                                                                            ##STR58##                                                      H                                                                                            ##STR59##                                                      H                                                                                            ##STR60##                                                      3-Cl                                                                                         ##STR61##                                                      4-Cl                                                                                         ##STR62##                                                      5-Cl                                                                                         ##STR63##                                                      H                                                                                            ##STR64##                                                      H                                                                                            ##STR65##                                                      H                                                                                            ##STR66##                                                      H                                                                                            ##STR67##                                                      H                                                                                            ##STR68##                                                      H                                                                                            ##STR69##                                                      H                                                                                            ##STR70##                                                      6-CH.sub.3 (CH.sub.2).sub.2 O                                                                ##STR71##                                                      H                                                                                            ##STR72##                                                      H                                                                                            ##STR73##                                                      H                                                                                            ##STR74##                                                      H                                                                                            ##STR75##                                                      H                                                                                            ##STR76##                                                      H                                                                                            ##STR77##                                                      H                                                                                            ##STR78##                                                      H                                                                                            ##STR79##                                                      ______________________________________                                    

                  TABLE III                                                       ______________________________________                                         ##STR80##                                                                    R.sub.1       R              m.p. °C.                                  ______________________________________                                                       ##STR81##     215-216                                          6-F                                                                                          ##STR82##                                                      6-Cl                                                                                         ##STR83##                                                      6-Br                                                                                         ##STR84##                                                      4-NO.sub.2                                                                                   ##STR85##                                                      6-CF.sub.3                                                                                   ##STR86##                                                      6-CH.sub.3                                                                                   ##STR87##                                                      4-CH.sub.3 (CH.sub.2).sub.3                                                                  ##STR88##                                                      6-CF.sub.3 O                                                                                 ##STR89##                                                      6-CH.sub.3 O                                                                                 ##STR90##                                                      4-CH.sub.3 (CH.sub.2).sub.3 O                                                                ##STR91##                                                      H                                                                                            ##STR92##                                                      H                                                                                            ##STR93##                                                      H                                                                                            ##STR94##                                                      H                                                                                            ##STR95##                                                      H                                                                                            ##STR96##                                                      3-Cl                                                                                         ##STR97##                                                      4-Cl                                                                                         ##STR98##                                                      5-Cl                                                                                         ##STR99##                                                      H                                                                                            ##STR100##                                                     H                                                                                            ##STR101##                                                     H                                                                                            ##STR102##                                                     H                                                                                            ##STR103##                                                     H                                                                                            ##STR104##                                                     H                                                                                            ##STR105##                                                     H                                                                                            ##STR106##                                                     6-CH.sub.3 (CH.sub.2).sub.2 O                                                                ##STR107##                                                     H                                                                                            ##STR108##                                                     H                                                                                            ##STR109##                                                     H                                                                                            ##STR110##                                                     H                                                                                            ##STR111##                                                     H                                                                                            ##STR112##                                                     H                                                                                            ##STR113##                                                     H                                                                                            ##STR114##                                                     H                                                                                            ##STR115##                                                     ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                         ##STR116##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR117##                                                 6-F                                                                                              ##STR118##                                                 6-Cl                                                                                             ##STR119##                                                 6-Br                                                                                             ##STR120##                                                 4-NO.sub.2                                                                                       ##STR121##                                                 6-CF.sub.3                                                                                       ##STR122##                                                 6-CH.sub.3                                                                                       ##STR123##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR124##                                                 6-CF.sub.3 O                                                                                     ##STR125##                                                 6-CH.sub.3 O                                                                                     ##STR126##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR127##                                                 H                                                                                                ##STR128##                                                 H                                                                                                ##STR129##                                                 H                                                                                                ##STR130##                                                 H                                                                                                ##STR131##                                                 H                                                                                                ##STR132##                                                 3-Cl                                                                                             ##STR133##                                                 4-Cl                                                                                             ##STR134##                                                 5-Cl                                                                                             ##STR135##                                                 H                                                                                                ##STR136##                                                 H                                                                                                ##STR137##                                                 H                                                                                                ##STR138##                                                 H                                                                                                ##STR139##                                                 H                                                                                                ##STR140##                                                 H                                                                                                ##STR141##                                                 H                                                                                                ##STR142##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR143##                                                 H                                                                                                ##STR144##                                                 H                                                                                                ##STR145##                                                 H                                                                                                ##STR146##                                                 H                                                                                                ##STR147##                                                 H                                                                                                ##STR148##                                                 H                                                                                                ##STR149##                                                 H                                                                                                ##STR150##                                                 H                                                                                                ##STR151##                                                 ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR152##                                                                   R.sub.1       R              m.p. °C.                                  ______________________________________                                                       ##STR153##                                                     6-F                                                                                          ##STR154##                                                     6-Cl                                                                                         ##STR155##    141° (dec)                                6-Br                                                                                         ##STR156##                                                     4-NO.sub.2                                                                                   ##STR157##                                                     6-CF.sub.3                                                                                   ##STR158##                                                     6-CH.sub.3                                                                                   ##STR159##                                                     4-CH.sub.3 (CH.sub. 2).sub.3                                                                 ##STR160##                                                     6-CF.sub.3 O                                                                                 ##STR161##                                                     6-CH.sub.3 O                                                                                 ##STR162##                                                     4-CH.sub.3 (CH.sub.2).sub.3 O                                                                ##STR163##                                                     H                                                                                            ##STR164##                                                     H                                                                                            ##STR165##                                                     H                                                                                            ##STR166##                                                     H                                                                                            ##STR167##                                                     H                                                                                            ##STR168##                                                     3-Cl                                                                                         ##STR169##                                                     4-Cl                                                                                         ##STR170##                                                     5-Cl                                                                                         ##STR171##                                                     H                                                                                            ##STR172##                                                     H                                                                                            ##STR173##                                                     H                                                                                            ##STR174##                                                     H                                                                                            ##STR175##                                                     H                                                                                            ##STR176##                                                     H                                                                                            ##STR177##                                                     H                                                                                            ##STR178##                                                     6-CH.sub.3 (CH.sub.2).sub.2 O                                                                ##STR179##                                                     H                                                                                            ##STR180##                                                     H                                                                                            ##STR181##                                                     H                                                                                            ##STR182##                                                     H                                                                                            ##STR183##                                                     H                                                                                            ##STR184##                                                     H                                                                                            ##STR185##                                                     H                                                                                            ##STR186##                                                     H                                                                                            ##STR187##                                                     ______________________________________                                    

                  TABLE VI                                                        ______________________________________                                         ##STR188##                                                                   R.sub.1       R              m.p. °C.                                  ______________________________________                                                       ##STR189##    167-172                                          6-F                                                                                          ##STR190##                                                     6-Cl                                                                                         ##STR191##                                                     6-Br                                                                                         ##STR192##                                                     4-NO.sub.2                                                                                   ##STR193##                                                     6-CF.sub.3                                                                                   ##STR194##                                                     6-CH.sub.3                                                                                   ##STR195##                                                     4-CH.sub.3 (CH.sub. 2).sub.3                                                                 ##STR196##                                                     6-CF.sub.3 O                                                                                 ##STR197##                                                     6-CH.sub.3 O                                                                                 ##STR198##                                                     4-CH.sub.3 (CH.sub.2).sub.3 O                                                                ##STR199##                                                     H                                                                                            ##STR200##                                                     H                                                                                            ##STR201##                                                     H                                                                                            ##STR202##                                                     H                                                                                            ##STR203##                                                     H                                                                                            ##STR204##                                                     3-Cl                                                                                         ##STR205##                                                     4-Cl                                                                                         ##STR206##                                                     5-Cl                                                                                         ##STR207##                                                     H                                                                                            ##STR208##                                                     H                                                                                            ##STR209##                                                     H                                                                                            ##STR210##                                                     H                                                                                            ##STR211##                                                     H                                                                                            ##STR212##                                                     H                                                                                            ##STR213##                                                     H                                                                                            ##STR214##                                                     6-CH.sub.3 (CH.sub.2).sub.2 O                                                                ##STR215##                                                     H                                                                                            ##STR216##                                                     H                                                                                            ##STR217##                                                     H                                                                                            ##STR218##                                                     H                                                                                            ##STR219##                                                     H                                                                                            ##STR220##                                                     H                                                                                            ##STR221##                                                     H                                                                                            ##STR222##                                                     H                                                                                            ##STR223##                                                     ______________________________________                                    

                  TABLE VII                                                       ______________________________________                                         ##STR224##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR225##                                                 6-F                                                                                              ##STR226##                                                 6-Cl                                                                                             ##STR227##                                                 6-Br                                                                                             ##STR228##                                                 4-NO.sub.2                                                                                       ##STR229##                                                 6-CF.sub.3                                                                                       ##STR230##                                                 6-CH.sub.3                                                                                       ##STR231##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR232##                                                 6-CF.sub.3 O                                                                                     ##STR233##                                                 6-CH.sub.3 O                                                                                     ##STR234##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR235##                                                 H                                                                                                ##STR236##                                                 H                                                                                                ##STR237##                                                 H                                                                                                ##STR238##                                                 H                                                                                                ##STR239##                                                 H                                                                                                ##STR240##                                                 3-Cl                                                                                             ##STR241##                                                 4-Cl                                                                                             ##STR242##                                                 5-Cl                                                                                             ##STR243##                                                 H                                                                                                ##STR244##                                                 H                                                                                                ##STR245##                                                 H                                                                                                ##STR246##                                                 H                                                                                                ##STR247##                                                 H                                                                                                ##STR248##                                                 H                                                                                                ##STR249##                                                 H                                                                                                ##STR250##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR251##                                                 H                                                                                                ##STR252##                                                 H                                                                                                ##STR253##                                                 H                                                                                                ##STR254##                                                 H                                                                                                ##STR255##                                                 H                                                                                                ##STR256##                                                 H                                                                                                ##STR257##                                                 H                                                                                                ##STR258##                                                 H                                                                                                ##STR259##                                                 ______________________________________                                    

                  TABLE VIII                                                      ______________________________________                                         ##STR260##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR261##                                                 6-F                                                                                              ##STR262##                                                 6-Cl                                                                                             ##STR263##                                                 6-Br                                                                                             ##STR264##                                                 4-NO.sub.2                                                                                       ##STR265##                                                 6-CF.sub.3                                                                                       ##STR266##                                                 6-CH.sub.3                                                                                       ##STR267##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR268##                                                 6-CF.sub.3 O                                                                                     ##STR269##                                                 6-CH.sub.3 O                                                                                     ##STR270##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR271##                                                 H                                                                                                ##STR272##                                                 H                                                                                                ##STR273##                                                 H                                                                                                ##STR274##                                                 H                                                                                                ##STR275##                                                 H                                                                                                ##STR276##                                                 3-Cl                                                                                             ##STR277##                                                 4-Cl                                                                                             ##STR278##                                                 5-Cl                                                                                             ##STR279##                                                 H                                                                                                ##STR280##                                                 H                                                                                                ##STR281##                                                 H                                                                                                ##STR282##                                                 H                                                                                                ##STR283##                                                 H                                                                                                ##STR284##                                                 H                                                                                                ##STR285##                                                 H                                                                                                ##STR286##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR287##                                                 H                                                                                                ##STR288##                                                 H                                                                                                ##STR289##                                                 H                                                                                                ##STR290##                                                 H                                                                                                ##STR291##                                                 H                                                                                                ##STR292##                                                 H                                                                                                ##STR293##                                                 H                                                                                                ##STR294##                                                 H                                                                                                ##STR295##                                                 ______________________________________                                    

                  TABLE IX                                                        ______________________________________                                         ##STR296##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR297##                                                 6-F                                                                                              ##STR298##                                                 6-Cl                                                                                             ##STR299##                                                 6-Br                                                                                             ##STR300##                                                 4-NO.sub.2                                                                                       ##STR301##                                                 6-CF.sub.3                                                                                       ##STR302##                                                 6-CH.sub.3                                                                                       ##STR303##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR304##                                                 6-CF.sub.3 O                                                                                     ##STR305##                                                 6-CH.sub.3 O                                                                                     ##STR306##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR307##                                                 H                                                                                                ##STR308##                                                 H                                                                                                ##STR309##                                                 H                                                                                                ##STR310##                                                 H                                                                                                ##STR311##                                                 H                                                                                                ##STR312##                                                 3-Cl                                                                                             ##STR313##                                                 4-Cl                                                                                             ##STR314##                                                 5-Cl                                                                                             ##STR315##                                                 H                                                                                                ##STR316##                                                 H                                                                                                ##STR317##                                                 H                                                                                                ##STR318##                                                 H                                                                                                ##STR319##                                                 H                                                                                                ##STR320##                                                 H                                                                                                ##STR321##                                                 H                                                                                                ##STR322##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR323##                                                 H                                                                                                ##STR324##                                                 H                                                                                                ##STR325##                                                 H                                                                                                ##STR326##                                                 H                                                                                                ##STR327##                                                 H                                                                                                ##STR328##                                                 H                                                                                                ##STR329##                                                 H                                                                                                ##STR330##                                                 H                                                                                                ##STR331##                                                 ______________________________________                                    

                  TABLE X                                                         ______________________________________                                         ##STR332##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR333##                                                 6-F                                                                                              ##STR334##                                                 6-Cl                                                                                             ##STR335##                                                 6-Br                                                                                             ##STR336##                                                 4-NO.sub.2                                                                                       ##STR337##                                                 6-CF.sub.3                                                                                       ##STR338##                                                 6-CH.sub.3                                                                                       ##STR339##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR340##                                                 6-CF.sub.3 O                                                                                     ##STR341##                                                 6-CH.sub.3 O                                                                                     ##STR342##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR343##                                                 H                                                                                                ##STR344##                                                 H                                                                                                ##STR345##                                                 H                                                                                                ##STR346##                                                 H                                                                                                ##STR347##                                                 H                                                                                                ##STR348##                                                 3-Cl                                                                                             ##STR349##                                                 4-Cl                                                                                             ##STR350##                                                 5-Cl                                                                                             ##STR351##                                                 H                                                                                                ##STR352##                                                 H                                                                                                ##STR353##                                                 H                                                                                                ##STR354##                                                 H                                                                                                ##STR355##                                                 H                                                                                                ##STR356##                                                 H                                                                                                ##STR357##                                                 H                                                                                                ##STR358##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR359##                                                 H                                                                                                ##STR360##                                                 H                                                                                                ##STR361##                                                 H                                                                                                ##STR362##                                                 H                                                                                                ##STR363##                                                 H                                                                                                ##STR364##                                                 H                                                                                                ##STR365##                                                 H                                                                                                ##STR366##                                                 H                                                                                                ##STR367##                                                 ______________________________________                                    

                  TABLE XI                                                        ______________________________________                                         ##STR368##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR369##                                                 6-F                                                                                              ##STR370##                                                 6-Cl                                                                                             ##STR371##                                                 6-Br                                                                                             ##STR372##                                                 4-NO.sub.2                                                                                       ##STR373##                                                 6-CF.sub.3                                                                                       ##STR374##                                                 6-CH.sub.3                                                                                       ##STR375##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR376##                                                 6-CF.sub.3 O                                                                                     ##STR377##                                                 6-CH.sub.3 O                                                                                     ##STR378##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR379##                                                 H                                                                                                ##STR380##                                                 H                                                                                                ##STR381##                                                 H                                                                                                ##STR382##                                                 H                                                                                                ##STR383##                                                 H                                                                                                ##STR384##                                                 3-Cl                                                                                             ##STR385##                                                 4-Cl                                                                                             ##STR386##                                                 5-Cl                                                                                             ##STR387##                                                 H                                                                                                ##STR388##                                                 H                                                                                                ##STR389##                                                 H                                                                                                ##STR390##                                                 H                                                                                                ##STR391##                                                 H                                                                                                ##STR392##                                                 H                                                                                                ##STR393##                                                 H                                                                                                ##STR394##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR395##                                                 H                                                                                                ##STR396##                                                 H                                                                                                ##STR397##                                                 H                                                                                                ##STR398##                                                 H                                                                                                ##STR399##                                                 H                                                                                                ##STR400##                                                 H                                                                                                ##STR401##                                                 H                                                                                                ##STR402##                                                 H                                                                                                ##STR403##                                                 ______________________________________                                    

                  TABLE XII                                                       ______________________________________                                         ##STR404##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR405##                                                 6-F                                                                                              ##STR406##                                                 6-Cl                                                                                             ##STR407##                                                 6-Br                                                                                             ##STR408##                                                 4-NO.sub.2                                                                                       ##STR409##                                                 6-CF.sub.3                                                                                       ##STR410##                                                 6-CH.sub.3                                                                                       ##STR411##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR412##                                                 6-CF.sub.3 O                                                                                     ##STR413##                                                 6-CH.sub.3 O                                                                                     ##STR414##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR415##                                                 H                                                                                                ##STR416##                                                 H                                                                                                ##STR417##                                                 H                                                                                                ##STR418##                                                 H                                                                                                ##STR419##                                                 H                                                                                                ##STR420##                                                 3-Cl                                                                                             ##STR421##                                                 4-Cl                                                                                             ##STR422##                                                 5-Cl                                                                                             ##STR423##                                                 H                                                                                                ##STR424##                                                 H                                                                                                ##STR425##                                                 H                                                                                                ##STR426##                                                 H                                                                                                ##STR427##                                                 H                                                                                                ##STR428##                                                 H                                                                                                ##STR429##                                                 H                                                                                                ##STR430##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR431##                                                 H                                                                                                ##STR432##                                                 H                                                                                                ##STR433##                                                 H                                                                                                ##STR434##                                                 H                                                                                                ##STR435##                                                 H                                                                                                ##STR436##                                                 H                                                                                                ##STR437##                                                 H                                                                                                ##STR438##                                                 H                                                                                                ##STR439##                                                 ______________________________________                                    

                  TABLE XIII                                                      ______________________________________                                         ##STR440##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR441##                                                 6-F                                                                                              ##STR442##                                                 6-Cl                                                                                             ##STR443##                                                 6-Br                                                                                             ##STR444##                                                 4-NO.sub.2                                                                                       ##STR445##                                                 6-CF.sub.3                                                                                       ##STR446##                                                 6-CH.sub.3                                                                                       ##STR447##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR448##                                                 6-CF.sub.3 O                                                                                     ##STR449##                                                 6-CH.sub.3 O                                                                                     ##STR450##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR451##                                                 H                                                                                                ##STR452##                                                 H                                                                                                ##STR453##                                                 H                                                                                                ##STR454##                                                 H                                                                                                ##STR455##                                                 H                                                                                                ##STR456##                                                 3-Cl                                                                                             ##STR457##                                                 4-Cl                                                                                             ##STR458##                                                 5-Cl                                                                                             ##STR459##                                                 H                                                                                                ##STR460##                                                 H                                                                                                ##STR461##                                                 H                                                                                                ##STR462##                                                 H                                                                                                ##STR463##                                                 H                                                                                                ##STR464##                                                 H                                                                                                ##STR465##                                                 H                                                                                                ##STR466##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR467##                                                 H                                                                                                ##STR468##                                                 H                                                                                                ##STR469##                                                 H                                                                                                ##STR470##                                                 H                                                                                                ##STR471##                                                 H                                                                                                ##STR472##                                                 H                                                                                                ##STR473##                                                 H                                                                                                ##STR474##                                                 H                                                                                                ##STR475##                                                 ______________________________________                                    

                  TABLE XIV                                                       ______________________________________                                         ##STR476##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR477##                                                 6-F                                                                                              ##STR478##                                                 6-Cl                                                                                             ##STR479##                                                 6-Br                                                                                             ##STR480##                                                 4-NO.sub.2                                                                                       ##STR481##                                                 6-CF.sub.3                                                                                       ##STR482##                                                 6-CH.sub.3                                                                                       ##STR483##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR484##                                                 6-CF.sub.3 O                                                                                     ##STR485##                                                 6-CH.sub.3 O                                                                                     ##STR486##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR487##                                                 H                                                                                                ##STR488##                                                 H                                                                                                ##STR489##                                                 H                                                                                                ##STR490##                                                 H                                                                                                ##STR491##                                                 H                                                                                                ##STR492##                                                 3-Cl                                                                                             ##STR493##                                                 4-Cl                                                                                             ##STR494##                                                 5-Cl                                                                                             ##STR495##                                                 H                                                                                                ##STR496##                                                 H                                                                                                ##STR497##                                                 H                                                                                                ##STR498##                                                 H                                                                                                ##STR499##                                                 H                                                                                                ##STR500##                                                 H                                                                                                ##STR501##                                                 H                                                                                                ##STR502##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR503##                                                 H                                                                                                ##STR504##                                                 H                                                                                                ##STR505##                                                 H                                                                                                ##STR506##                                                 H                                                                                                ##STR507##                                                 H                                                                                                ##STR508##                                                 H                                                                                                ##STR509##                                                 H                                                                                                ##STR510##                                                 H                                                                                                ##STR511##                                                 ______________________________________                                    

                  TABLE XV                                                        ______________________________________                                         ##STR512##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR513##                                                 6-F                                                                                              ##STR514##                                                 6-Cl                                                                                             ##STR515##                                                 6-Br                                                                                             ##STR516##                                                 4-NO.sub.2                                                                                       ##STR517##                                                 6-CF.sub.3                                                                                       ##STR518##                                                 6-CH.sub.3                                                                                       ##STR519##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR520##                                                 6-CF.sub.3 O                                                                                     ##STR521##                                                 6-CH.sub.3 O                                                                                     ##STR522##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR523##                                                 H                                                                                                ##STR524##                                                 H                                                                                                ##STR525##                                                 H                                                                                                ##STR526##                                                 H                                                                                                ##STR527##                                                 H                                                                                                ##STR528##                                                 3-Cl                                                                                             ##STR529##                                                 4-Cl                                                                                             ##STR530##                                                 5-Cl                                                                                             ##STR531##                                                 H                                                                                                ##STR532##                                                 H                                                                                                ##STR533##                                                 H                                                                                                ##STR534##                                                 H                                                                                                ##STR535##                                                 H                                                                                                ##STR536##                                                 H                                                                                                ##STR537##                                                 H                                                                                                ##STR538##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR539##                                                 H                                                                                                ##STR540##                                                 H                                                                                                ##STR541##                                                 H                                                                                                ##STR542##                                                 H                                                                                                ##STR543##                                                 H                                                                                                ##STR544##                                                 H                                                                                                ##STR545##                                                 H                                                                                                ##STR546##                                                 H                                                                                                ##STR547##                                                 ______________________________________                                    

                  TABLE XVI                                                       ______________________________________                                         ##STR548##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR549##                                                 6-F                                                                                              ##STR550##                                                 6-Cl                                                                                             ##STR551##                                                 6-Br                                                                                             ##STR552##                                                 4-NO.sub.2                                                                                       ##STR553##                                                 6-CF.sub.3                                                                                       ##STR554##                                                 6-CH.sub.3                                                                                       ##STR555##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR556##                                                 6-CF.sub.3 O                                                                                     ##STR557##                                                 6-CH.sub.3 O                                                                                     ##STR558##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR559##                                                 H                                                                                                ##STR560##                                                 H                                                                                                ##STR561##                                                 H                                                                                                ##STR562##                                                 H                                                                                                ##STR563##                                                 H                                                                                                ##STR564##                                                 3-Cl                                                                                             ##STR565##                                                 4-Cl                                                                                             ##STR566##                                                 5-Cl                                                                                             ##STR567##                                                 H                                                                                                ##STR568##                                                 H                                                                                                ##STR569##                                                 H                                                                                                ##STR570##                                                 H                                                                                                ##STR571##                                                 H                                                                                                ##STR572##                                                 H                                                                                                ##STR573##                                                 H                                                                                                ##STR574##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR575##                                                 H                                                                                                ##STR576##                                                 H                                                                                                ##STR577##                                                 H                                                                                                ##STR578##                                                 H                                                                                                ##STR579##                                                 H                                                                                                ##STR580##                                                 H                                                                                                ##STR581##                                                 H                                                                                                ##STR582##                                                 H                                                                                                ##STR583##                                                 ______________________________________                                    

                  TABLE XVII                                                      ______________________________________                                         ##STR584##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR585##                                                 6-F                                                                                              ##STR586##                                                 6-Cl                                                                                             ##STR587##                                                 6-Br                                                                                             ##STR588##                                                 4-NO.sub.2                                                                                       ##STR589##                                                 6-CF.sub.3                                                                                       ##STR590##                                                 6-CH.sub.3                                                                                       ##STR591##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR592##                                                 6-CF.sub.3 O                                                                                     ##STR593##                                                 6-CH.sub.3 O                                                                                     ##STR594##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR595##                                                 H                                                                                                ##STR596##                                                 H                                                                                                ##STR597##                                                 H                                                                                                ##STR598##                                                 H                                                                                                ##STR599##                                                 H                                                                                                ##STR600##                                                 3-Cl                                                                                             ##STR601##                                                 4-Cl                                                                                             ##STR602##                                                 5-Cl                                                                                             ##STR603##                                                 H                                                                                                ##STR604##                                                 H                                                                                                ##STR605##                                                 H                                                                                                ##STR606##                                                 H                                                                                                ##STR607##                                                 H                                                                                                ##STR608##                                                 H                                                                                                ##STR609##                                                 H                                                                                                ##STR610##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR611##                                                 H                                                                                                ##STR612##                                                 H                                                                                                ##STR613##                                                 H                                                                                                ##STR614##                                                 H                                                                                                ##STR615##                                                 H                                                                                                ##STR616##                                                 H                                                                                                ##STR617##                                                 H                                                                                                ##STR618##                                                 H                                                                                                ##STR619##                                                 ______________________________________                                    

                  TABLE XVIII                                                     ______________________________________                                         ##STR620##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR621##                                                 6-F                                                                                              ##STR622##                                                 6-Cl                                                                                             ##STR623##                                                 6-Br                                                                                             ##STR624##                                                 4-NO.sub.2                                                                                       ##STR625##                                                 6-CF.sub.3                                                                                       ##STR626##                                                 6-CH.sub.3                                                                                       ##STR627##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR628##                                                 6-CF.sub.3 O                                                                                     ##STR629##                                                 6-CH.sub.3 O                                                                                     ##STR630##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR631##                                                 H                                                                                                ##STR632##                                                 H                                                                                                ##STR633##                                                 H                                                                                                ##STR634##                                                 H                                                                                                ##STR635##                                                 H                                                                                                ##STR636##                                                 3-Cl                                                                                             ##STR637##                                                 4-Cl                                                                                             ##STR638##                                                 5-Cl                                                                                             ##STR639##                                                 H                                                                                                ##STR640##                                                 H                                                                                                ##STR641##                                                 H                                                                                                ##STR642##                                                 H                                                                                                ##STR643##                                                 H                                                                                                ##STR644##                                                 H                                                                                                ##STR645##                                                 H                                                                                                ##STR646##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR647##                                                 H                                                                                                ##STR648##                                                 H                                                                                                ##STR649##                                                 H                                                                                                ##STR650##                                                 H                                                                                                ##STR651##                                                 H                                                                                                ##STR652##                                                 H                                                                                                ##STR653##                                                 H                                                                                                ##STR654##                                                 H                                                                                                ##STR655##                                                 ______________________________________                                    

                  TABLE XIX                                                       ______________________________________                                         ##STR656##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR657##                                                 6-F                                                                                              ##STR658##                                                 6-Cl                                                                                             ##STR659##                                                 6-Br                                                                                             ##STR660##                                                 4-NO.sub.2                                                                                       ##STR661##                                                 6-CF.sub.3                                                                                       ##STR662##                                                 6-CH.sub.3                                                                                       ##STR663##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR664##                                                 6-CF.sub.3 O                                                                                     ##STR665##                                                 6-CH.sub.3 O                                                                                     ##STR666##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR667##                                                 H                                                                                                ##STR668##                                                 H                                                                                                ##STR669##                                                 H                                                                                                ##STR670##                                                 H                                                                                                ##STR671##                                                 H                                                                                                ##STR672##                                                 3-Cl                                                                                             ##STR673##                                                 4-Cl                                                                                             ##STR674##                                                 5-Cl                                                                                             ##STR675##                                                 H                                                                                                ##STR676##                                                 H                                                                                                ##STR677##                                                 H                                                                                                ##STR678##                                                 H                                                                                                ##STR679##                                                 H                                                                                                ##STR680##                                                 H                                                                                                ##STR681##                                                 H                                                                                                ##STR682##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR683##                                                 H                                                                                                ##STR684##                                                 H                                                                                                ##STR685##                                                 H                                                                                                ##STR686##                                                 H                                                                                                ##STR687##                                                 H                                                                                                ##STR688##                                                 H                                                                                                ##STR689##                                                 H                                                                                                ##STR690##                                                 H                                                                                                ##STR691##                                                 ______________________________________                                    

                  TABLE XX                                                        ______________________________________                                         ##STR692##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR693##                                                 6-F                                                                                              ##STR694##                                                 6-Cl                                                                                             ##STR695##                                                 6-Br                                                                                             ##STR696##                                                 4-NO.sub.2                                                                                       ##STR697##                                                 6-CF.sub.3                                                                                       ##STR698##                                                 6-CH.sub.3                                                                                       ##STR699##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR700##                                                 6-CF.sub.3 O                                                                                     ##STR701##                                                 6-CH.sub.3 O                                                                                     ##STR702##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR703##                                                 H                                                                                                ##STR704##                                                 H                                                                                                ##STR705##                                                 H                                                                                                ##STR706##                                                 H                                                                                                ##STR707##                                                 H                                                                                                ##STR708##                                                 3-Cl                                                                                             ##STR709##                                                 4-Cl                                                                                             ##STR710##                                                 5-Cl                                                                                             ##STR711##                                                 H                                                                                                ##STR712##                                                 H                                                                                                ##STR713##                                                 H                                                                                                ##STR714##                                                 H                                                                                                ##STR715##                                                 H                                                                                                ##STR716##                                                 H                                                                                                ##STR717##                                                 H                                                                                                ##STR718##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR719##                                                 H                                                                                                ##STR720##                                                 H                                                                                                ##STR721##                                                 H                                                                                                ##STR722##                                                 H                                                                                                ##STR723##                                                 H                                                                                                ##STR724##                                                 H                                                                                                ##STR725##                                                 H                                                                                                ##STR726##                                                 H                                                                                                ##STR727##                                                 ______________________________________                                    

                  TABLE XXI                                                       ______________________________________                                         ##STR728##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR729##                                                 6-F                                                                                              ##STR730##                                                 6-Cl                                                                                             ##STR731##                                                 6-Br                                                                                             ##STR732##                                                 4-NO.sub.2                                                                                       ##STR733##                                                 6-CF.sub.3                                                                                       ##STR734##                                                 6-CH.sub.3                                                                                       ##STR735##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR736##                                                 6-CF.sub.3 O                                                                                     ##STR737##                                                 6-CH.sub.3 O                                                                                     ##STR738##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR739##                                                 H                                                                                                ##STR740##                                                 H                                                                                                ##STR741##                                                 H                                                                                                ##STR742##                                                 H                                                                                                ##STR743##                                                 H                                                                                                ##STR744##                                                 3-Cl                                                                                             ##STR745##                                                 4-Cl                                                                                             ##STR746##                                                 5-Cl                                                                                             ##STR747##                                                 H                                                                                                ##STR748##                                                 H                                                                                                ##STR749##                                                 H                                                                                                ##STR750##                                                 H                                                                                                ##STR751##                                                 H                                                                                                ##STR752##                                                 H                                                                                                ##STR753##                                                 H                                                                                                ##STR754##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR755##                                                 H                                                                                                ##STR756##                                                 H                                                                                                ##STR757##                                                 H                                                                                                ##STR758##                                                 H                                                                                                ##STR759##                                                 H                                                                                                ##STR760##                                                 H                                                                                                ##STR761##                                                 H                                                                                                ##STR762##                                                 H                                                                                                ##STR763##                                                 ______________________________________                                    

                  TABLE XXII                                                      ______________________________________                                         ##STR764##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR765##                                                 6-F                                                                                              ##STR766##                                                 6-Cl                                                                                             ##STR767##                                                 6-Br                                                                                             ##STR768##                                                 4-NO.sub.2                                                                                       ##STR769##                                                 6-CF.sub.3                                                                                       ##STR770##                                                 6-CH.sub.3                                                                                       ##STR771##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR772##                                                 6-CF.sub.3 O                                                                                     ##STR773##                                                 6-CH.sub.3 O                                                                                     ##STR774##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR775##                                                 H                                                                                                ##STR776##                                                 H                                                                                                ##STR777##                                                 H                                                                                                ##STR778##                                                 H                                                                                                ##STR779##                                                 H                                                                                                ##STR780##                                                 3-Cl                                                                                             ##STR781##                                                 4-Cl                                                                                             ##STR782##                                                 5-Cl                                                                                             ##STR783##                                                 H                                                                                                ##STR784##                                                 H                                                                                                ##STR785##                                                 H                                                                                                ##STR786##                                                 H                                                                                                ##STR787##                                                 H                                                                                                ##STR788##                                                 H                                                                                                ##STR789##                                                 H                                                                                                ##STR790##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR791##                                                 H                                                                                                ##STR792##                                                 H                                                                                                ##STR793##                                                 H                                                                                                ##STR794##                                                 H                                                                                                ##STR795##                                                 H                                                                                                ##STR796##                                                 H                                                                                                ##STR797##                                                 H                                                                                                ##STR798##                                                 H                                                                                                ##STR799##                                                 ______________________________________                                    

                  TABLE XXIII                                                     ______________________________________                                         ##STR800##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR801##                                                 6-F                                                                                              ##STR802##                                                 6-Cl                                                                                             ##STR803##                                                 6-Br                                                                                             ##STR804##                                                 4-NO.sub.2                                                                                       ##STR805##                                                 6-CF.sub.3                                                                                       ##STR806##                                                 6-CH.sub.3                                                                                       ##STR807##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR808##                                                 6-CF.sub.3 O                                                                                     ##STR809##                                                 6-CH.sub.3 O                                                                                     ##STR810##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR811##                                                 H                                                                                                ##STR812##                                                 H                                                                                                ##STR813##                                                 H                                                                                                ##STR814##                                                 H                                                                                                ##STR815##                                                 H                                                                                                ##STR816##                                                 3-Cl                                                                                             ##STR817##                                                 4-Cl                                                                                             ##STR818##                                                 5-Cl                                                                                             ##STR819##                                                 H                                                                                                ##STR820##                                                 H                                                                                                ##STR821##                                                 H                                                                                                ##STR822##                                                 H                                                                                                ##STR823##                                                 H                                                                                                ##STR824##                                                 H                                                                                                ##STR825##                                                 H                                                                                                ##STR826##                                                 6-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR827##                                                 H                                                                                                ##STR828##                                                 H                                                                                                ##STR829##                                                 H                                                                                                ##STR830##                                                 H                                                                                                ##STR831##                                                 H                                                                                                ##STR832##                                                 H                                                                                                ##STR833##                                                 H                                                                                                ##STR834##                                                 H                                                                                                ##STR835##                                                 ______________________________________                                    

                  TABLE XXIV                                                      ______________________________________                                         ##STR836##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR837##                                                 6-F                                                                                              ##STR838##                                                 6-Cl                                                                                             ##STR839##                                                 6-Br                                                                                             ##STR840##                                                 4-NO.sub.2                                                                                       ##STR841##                                                 6-CF.sub.3                                                                                       ##STR842##                                                 6-CH.sub.3                                                                                       ##STR843##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR844##                                                 6-CF.sub.3 O                                                                                     ##STR845##                                                 6-CH.sub.3 O                                                                                     ##STR846##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR847##                                                 H                                                                                                ##STR848##                                                 H                                                                                                ##STR849##                                                 H                                                                                                ##STR850##                                                 H                                                                                                ##STR851##                                                 H                                                                                                ##STR852##                                                 3-Cl                                                                                             ##STR853##                                                 4-Cl                                                                                             ##STR854##                                                 5-Cl                                                                                             ##STR855##                                                 H                                                                                                ##STR856##                                                 H                                                                                                ##STR857##                                                 H                                                                                                ##STR858##                                                 H                                                                                                ##STR859##                                                 H                                                                                                ##STR860##                                                 H                                                                                                ##STR861##                                                 H                                                                                                ##STR862##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR863##                                                 H                                                                                                ##STR864##                                                 H                                                                                                ##STR865##                                                 H                                                                                                ##STR866##                                                 H                                                                                                ##STR867##                                                 H                                                                                                ##STR868##                                                 H                                                                                                ##STR869##                                                 H                                                                                                ##STR870##                                                 H                                                                                                ##STR871##                                                 ______________________________________                                    

                  TABLE XXV                                                       ______________________________________                                         ##STR872##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR873##                                                 6-F                                                                                              ##STR874##                                                 6-Cl                                                                                             ##STR875##                                                 6-Br                                                                                             ##STR876##                                                 4-NO.sub.2                                                                                       ##STR877##                                                 6-CF.sub.3                                                                                       ##STR878##                                                 6-CH.sub.3                                                                                       ##STR879##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR880##                                                 6-CF.sub.3 O                                                                                     ##STR881##                                                 6-CH.sub.3 O                                                                                     ##STR882##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR883##                                                 H                                                                                                ##STR884##                                                 H                                                                                                ##STR885##                                                 H                                                                                                ##STR886##                                                 H                                                                                                ##STR887##                                                 H                                                                                                ##STR888##                                                 3-Cl                                                                                             ##STR889##                                                 4-Cl                                                                                             ##STR890##                                                 5-Cl                                                                                             ##STR891##                                                 H                                                                                                ##STR892##                                                 H                                                                                                ##STR893##                                                 H                                                                                                ##STR894##                                                 H                                                                                                ##STR895##                                                 H                                                                                                ##STR896##                                                 H                                                                                                ##STR897##                                                 H                                                                                                ##STR898##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR899##                                                 H                                                                                                ##STR900##                                                 H                                                                                                ##STR901##                                                 H                                                                                                ##STR902##                                                 H                                                                                                ##STR903##                                                 H                                                                                                ##STR904##                                                 H                                                                                                ##STR905##                                                 H                                                                                                ##STR906##                                                 H                                                                                                ##STR907##                                                 ______________________________________                                    

                  TABLE XXVI                                                      ______________________________________                                         ##STR908##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR909##                                                 6-F                                                                                              ##STR910##                                                 6-Cl                                                                                             ##STR911##                                                 6-Br                                                                                             ##STR912##                                                 4-NO.sub.2                                                                                       ##STR913##                                                 6-CF.sub.3                                                                                       ##STR914##                                                 6-CH.sub.3                                                                                       ##STR915##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR916##                                                 6-CF.sub.3 O                                                                                     ##STR917##                                                 6-CH.sub.3 O                                                                                     ##STR918##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR919##                                                 H                                                                                                ##STR920##                                                 H                                                                                                ##STR921##                                                 H                                                                                                ##STR922##                                                 H                                                                                                ##STR923##                                                 H                                                                                                ##STR924##                                                 3-Cl                                                                                             ##STR925##                                                 4-Cl                                                                                             ##STR926##                                                 5-Cl                                                                                             ##STR927##                                                 H                                                                                                ##STR928##                                                 H                                                                                                ##STR929##                                                 H                                                                                                ##STR930##                                                 H                                                                                                ##STR931##                                                 H                                                                                                ##STR932##                                                 H                                                                                                ##STR933##                                                 H                                                                                                ##STR934##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR935##                                                 H                                                                                                ##STR936##                                                 H                                                                                                ##STR937##                                                 H                                                                                                ##STR938##                                                 H                                                                                                ##STR939##                                                 H                                                                                                ##STR940##                                                 H                                                                                                ##STR941##                                                 H                                                                                                ##STR942##                                                 H                                                                                                ##STR943##                                                 ______________________________________                                    

                  TABLE XXVII                                                     ______________________________________                                         ##STR944##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR945##                                                 6-F                                                                                              ##STR946##                                                 6-Cl                                                                                             ##STR947##                                                 6-Br                                                                                             ##STR948##                                                 4-NO.sub.2                                                                                       ##STR949##                                                 6-CF.sub.3                                                                                       ##STR950##                                                 6-CH.sub.3                                                                                       ##STR951##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR952##                                                 6-CF.sub.3 O                                                                                     ##STR953##                                                 6-CH.sub.3 O                                                                                     ##STR954##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR955##                                                 H                                                                                                ##STR956##                                                 H                                                                                                ##STR957##                                                 H                                                                                                ##STR958##                                                 H                                                                                                ##STR959##                                                 H                                                                                                ##STR960##                                                 3-Cl                                                                                             ##STR961##                                                 4-Cl                                                                                             ##STR962##                                                 5-Cl                                                                                             ##STR963##                                                 H                                                                                                ##STR964##                                                 H                                                                                                ##STR965##                                                 H                                                                                                ##STR966##                                                 H                                                                                                ##STR967##                                                 H                                                                                                ##STR968##                                                 H                                                                                                ##STR969##                                                 H                                                                                                ##STR970##                                                 6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR971##                                                 H                                                                                                ##STR972##                                                 H                                                                                                ##STR973##                                                 H                                                                                                ##STR974##                                                 H                                                                                                ##STR975##                                                 H                                                                                                ##STR976##                                                 H                                                                                                ##STR977##                                                 H                                                                                                ##STR978##                                                 H                                                                                                ##STR979##                                                 ______________________________________                                    

                  TABLE XXVIII                                                    ______________________________________                                         ##STR980##                                                                   R.sub.1           R                                                           ______________________________________                                                           ##STR981##                                                 6-F                                                                                              ##STR982##                                                 6-Cl                                                                                             ##STR983##                                                 6-Br                                                                                             ##STR984##                                                 4-NO.sub.2                                                                                       ##STR985##                                                 6-CF.sub.3                                                                                       ##STR986##                                                 6-CH.sub.3                                                                                       ##STR987##                                                 4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR988##                                                 6-CF.sub.3 O                                                                                     ##STR989##                                                 6-CH.sub.3 O                                                                                     ##STR990##                                                 4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR991##                                                 H                                                                                                ##STR992##                                                 H                                                                                                ##STR993##                                                 H                                                                                                ##STR994##                                                 H                                                                                                ##STR995##                                                 H                                                                                                ##STR996##                                                 3-Cl                                                                                             ##STR997##                                                 4-Cl                                                                                             ##STR998##                                                 5-Cl                                                                                             ##STR999##                                                 H                                                                                                ##STR1000##                                                H                                                                                                ##STR1001##                                                H                                                                                                ##STR1002##                                                H                                                                                                ##STR1003##                                                H                                                                                                ##STR1004##                                                H                                                                                                ##STR1005##                                                H                                                                                                ##STR1006##                                                6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR1007##                                                H                                                                                                ##STR1008##                                                H                                                                                                ##STR1009##                                                H                                                                                                ##STR1010##                                                H                                                                                                ##STR1011##                                                H                                                                                                ##STR1012##                                                H                                                                                                ##STR1013##                                                H                                                                                                ##STR1014##                                                H                                                                                                ##STR1015##                                                ______________________________________                                    

                  TABLE XXIX                                                      ______________________________________                                         ##STR1016##                                                                  R.sub.1           R                                                           ______________________________________                                                           ##STR1017##                                                6-F                                                                                              ##STR1018##                                                6-Cl                                                                                             ##STR1019##                                                6-Br                                                                                             ##STR1020##                                                4-NO.sub.2                                                                                       ##STR1021##                                                6-CF.sub.3                                                                                       ##STR1022##                                                6-CH.sub.3                                                                                       ##STR1023##                                                4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR1024##                                                6-CF.sub.3 O                                                                                     ##STR1025##                                                6-CH.sub.3 O                                                                                     ##STR1026##                                                4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR1027##                                                H                                                                                                ##STR1028##                                                H                                                                                                ##STR1029##                                                H                                                                                                ##STR1030##                                                H                                                                                                ##STR1031##                                                H                                                                                                ##STR1032##                                                3-Cl                                                                                             ##STR1033##                                                4-Cl                                                                                             ##STR1034##                                                5-Cl                                                                                             ##STR1035##                                                H                                                                                                ##STR1036##                                                H                                                                                                ##STR1037##                                                H                                                                                                ##STR1038##                                                H                                                                                                ##STR1039##                                                H                                                                                                ##STR1040##                                                H                                                                                                ##STR1041##                                                H                                                                                                ##STR1042##                                                6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR1043##                                                H                                                                                                ##STR1044##                                                H                                                                                                ##STR1045##                                                H                                                                                                ##STR1046##                                                H                                                                                                ##STR1047##                                                H                                                                                                ##STR1048##                                                H                                                                                                ##STR1049##                                                H                                                                                                ##STR1050##                                                H                                                                                                ##STR1051##                                                ______________________________________                                    

                  TABLE XXX                                                       ______________________________________                                         ##STR1052##                                                                  R.sub.1           R                                                           ______________________________________                                                           ##STR1053##                                                6-F                                                                                              ##STR1054##                                                6-Cl                                                                                             ##STR1055##                                                6-Br                                                                                             ##STR1056##                                                4-NO.sub.2                                                                                       ##STR1057##                                                6-CF.sub.3                                                                                       ##STR1058##                                                6-CH.sub.3                                                                                       ##STR1059##                                                4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR1060##                                                6-CF.sub.3 O                                                                                     ##STR1061##                                                6-CH.sub.3 O                                                                                     ##STR1062##                                                4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR1063##                                                H                                                                                                ##STR1064##                                                H                                                                                                ##STR1065##                                                H                                                                                                ##STR1066##                                                H                                                                                                ##STR1067##                                                H                                                                                                ##STR1068##                                                3-Cl                                                                                             ##STR1069##                                                4-Cl                                                                                             ##STR1070##                                                5-Cl                                                                                             ##STR1071##                                                H                                                                                                ##STR1072##                                                H                                                                                                ##STR1073##                                                H                                                                                                ##STR1074##                                                H                                                                                                ##STR1075##                                                H                                                                                                ##STR1076##                                                H                                                                                                ##STR1077##                                                H                                                                                                ##STR1078##                                                6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR1079##                                                H                                                                                                ##STR1080##                                                H                                                                                                ##STR1081##                                                H                                                                                                ##STR1082##                                                H                                                                                                ##STR1083##                                                H                                                                                                ##STR1084##                                                H                                                                                                ##STR1085##                                                H                                                                                                ##STR1086##                                                H                                                                                                ##STR1087##                                                ______________________________________                                    

                  TABLE XXXI                                                      ______________________________________                                         ##STR1088##                                                                  R.sub.1           R                                                           ______________________________________                                                           ##STR1089##                                                6-F                                                                                              ##STR1090##                                                6-Cl                                                                                             ##STR1091##                                                6-Br                                                                                             ##STR1092##                                                4-NO.sub.2                                                                                       ##STR1093##                                                6-CF.sub.3                                                                                       ##STR1094##                                                6-CH.sub.3                                                                                       ##STR1095##                                                4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR1096##                                                6-CF.sub.3 O                                                                                     ##STR1097##                                                6-CH.sub.3 O                                                                                     ##STR1098##                                                4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR1099##                                                H                                                                                                ##STR1100##                                                H                                                                                                ##STR1101##                                                H                                                                                                ##STR1102##                                                H                                                                                                ##STR1103##                                                H                                                                                                ##STR1104##                                                3-Cl                                                                                             ##STR1105##                                                4-Cl                                                                                             ##STR1106##                                                5-Cl                                                                                             ##STR1107##                                                H                                                                                                ##STR1108##                                                H                                                                                                ##STR1109##                                                H                                                                                                ##STR1110##                                                H                                                                                                ##STR1111##                                                H                                                                                                ##STR1112##                                                H                                                                                                ##STR1113##                                                H                                                                                                ##STR1114##                                                6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR1115##                                                H                                                                                                ##STR1116##                                                H                                                                                                ##STR1117##                                                H                                                                                                ##STR1118##                                                H                                                                                                ##STR1119##                                                H                                                                                                ##STR1120##                                                H                                                                                                ##STR1121##                                                H                                                                                                ##STR1122##                                                H                                                                                                ##STR1123##                                                ______________________________________                                    

                  TABLE XXXII                                                     ______________________________________                                         ##STR1124##                                                                  R.sub.1           R                                                           ______________________________________                                                           ##STR1125##                                                6-F                                                                                              ##STR1126##                                                6-Cl                                                                                             ##STR1127##                                                6-Br                                                                                             ##STR1128##                                                4-NO.sub.2                                                                                       ##STR1129##                                                6-CF.sub.3                                                                                       ##STR1130##                                                6-CH.sub.3                                                                                       ##STR1131##                                                4-CH.sub.3 (CH.sub.2).sub.3                                                                      ##STR1132##                                                6-CF.sub.3 O                                                                                     ##STR1133##                                                6-CH.sub.3 O                                                                                     ##STR1134##                                                4-CH.sub.3 (CH.sub.2).sub.3 O                                                                    ##STR1135##                                                H                                                                                                ##STR1136##                                                H                                                                                                ##STR1137##                                                H                                                                                                ##STR1138##                                                H                                                                                                ##STR1139##                                                H                                                                                                ##STR1140##                                                3-Cl                                                                                             ##STR1141##                                                4-Cl                                                                                             ##STR1142##                                                5-Cl                                                                                             ##STR1143##                                                H                                                                                                ##STR1144##                                                H                                                                                                ##STR1145##                                                H                                                                                                ##STR1146##                                                H                                                                                                ##STR1147##                                                H                                                                                                ##STR1148##                                                H                                                                                                ##STR1149##                                                H                                                                                                ##STR1150##                                                6-CH.sub.3 (CH.sub.2).sub.2 O                                                                    ##STR1151##                                                H                                                                                                ##STR1152##                                                H                                                                                                ##STR1153##                                                H                                                                                                ##STR1154##                                                H                                                                                                ##STR1155##                                                H                                                                                                ##STR1156##                                                H                                                                                                ##STR1157##                                                H                                                                                                ##STR1158##                                                H                                                                                                ##STR1159##                                                ______________________________________                                    

EXAMPLE 13,2'-Dichloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide

a. 3,2'-Dichloro-[1,1'-biphenyl]-2-sulfonyl chloride

To 588 ml of concentrated HCl and 196 ml of water at 0° to 10° wasadded, dropwise, 250 g of 2-chloroaniline. The mixture was purged withnitrogen and treated during a 1-hour period at 0° to 5° with a solutionof 147 g of sodium nitrite in 294 ml of water. After 0.5 hour at 5° to10° and 1.2 hour at 0° to 10°, the mixture was treated with 784 ml ofcold (5° to 10°) concentrated HCl, then sparged with nitrogen forseveral minutes. Then, 55 ml of liquid SO₂ was added to the reactionmixture at 10°, followed by 15.4 g of anhydrous cupric chloride at 15°and the mixture was stirred slowly overnight. The heavy oil was drawnoff, the aqueous layer extracted with butyl chloride and the combinedorganic portions washed with water (twice), half-saturated sodiumbicarbonate solution (until the washings were basic) and saturatedbrine, then dried over MgSO₄, treated with activated carbon andfiltered. The filtrate was evaporated to a deep-red oil andvacuum-distilled to remove material boiling up to 119° at 0.1 Torr. Thepot residue was dissolved in butyl chloride, filtered through silica geland the filtrate evaporated to provide an oil, which wasvacuum-distilled. The fraction boiling at 180°-196°/(0.7-1.0 Torr) waschromatographed on a column of silica gel with butyl chloride/hexane 1:6to 1:4 volume ratio) to provide, after evaporation of solvent, thesulfonyl chloride as an orange oil (Rf≈0.58 on a silica gel-coated TLCplate with butyl chloride/hexane, 1:6 v/v, eluent); gaschromatography/mass spectral analysis indicates an approximate 95%purity. NMR confirmed the isomeric structure indicated.

b. 3,2'-Dichloro-[1,1'-biphenyl]-2-sulfonamide

A tetrahydrofuran (THF) solution of 1.57 g of the sulfonyl chloride(from a) was sparged with ammonia. The mixture was then diluted withwater, the aqueous layer decanted, and the residual white solid filteredoff and washed with butyl chloride. The solid was dissolved in hot ethylacetate, the solution dried (MgSO₄) and diluted with hexane toprecipitate the desired sulfonamide, 1.33 g (90% yield), m.p. 151°-153°.

c. 3,2'-Dichloro-[1,1'-biphenyl]-2-sulfonyl isocyanate

The sulfonamide (from b) was dissolved in 40 ml of thionyl chloride andrefluxed for 42 hours. Evaporation of the unreacted thionyl chlorideyielded the N-sulfinylsulfonamide as a yellow oil. The oil was contactedwith 10 ml of a 13.8% phosgene solution in toluene, and a drop ofpyridine, and was heated (under a dry-ice condenser) on a steam bath for1.7 hours. The mixture was evaporated and the residue dissolved inacetonitrile and filtered. A sample of the acetonitrile solution wasevaporated to a gum which was treated with a little methylene chlorideand an infrared spectrum taken of the thus-thinned gum. The isocyanatepresence was confirmed by the strong absorption peak at 2230 cm⁻¹.

d.3,2'-Dichloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide

The acetonitrile solution of the sulfonyl isocyanate (from c) wastreated with 0.7 g of 2-amino-4-methoxy-6-methyl-s-triazine and themixture stirred at ambient temperature for 18 hours. The white solid wasfiltered off and the filtrate evaporated to a tacky solid, which was thetitle sulfonylurea. This product was further purified by triturationwith butyl chloride, dissolution in THF and precipitation from the THFsolution by dilution with 0.5 N HCl. The solid was redissolved in THF.The butyl chloride solution obtained in the earlier trituration wasevaporated, the residue dissolved in THF and precipitated by dilution ofthe THF solution with 0.5 N HCl; the precipitate was dried, boiled withbutyl chloride; the butyl chloride mixture was then filtered and thefilutrate diluted with hexane to precipitate a white solid. This solidwas dissolved in THF, the solution combined with the THF solutionobtained earlier and evaporated. The residue was washed with butylchloride and hexane leaving the title sulfonylurea as 1.17 g of whitesolid, m.p. 141° (dec). The IR spectrum showed absorption at 1720 cm⁻ 1consistent with the urea carbonyl group.

EXAMPLE 2a 1,1'-Biphenyl-2-sulfonyl isocyanate

Into a dry, 500 ml, 3 neck round bottom flask, equipped with adry-ice-cooled reflux condenser, stirrer, gas inlet tube and thermometerwas charged 12 g of 1,1'-biphenyl-2-sulfonamide, 100 ml of xylene, 0.2 gof 1,4-diaza[2.2.2]bicyclooctane (DABCO) and 5 g of n-butyl isocyanate.The mixture was heated to 135° and then phosgene was passed into thesystem until the temperature dropped to 125°. Heating was continued tobring the mixture up to 135° and additional phosgene was added to lowerthe temperature to 120°. This cycling was repeated until the temperatureof the refluxing mixture remained at 120° without further addition ofphosgene. The mixture was then allowed to cool to room temperature,filtered and concentrated in vacuo. Any contact with moisture wasscrupulously avoided due to the extreme reactivity of the sulfonylisocyanate. The product thus obtained (yield 10.4 g) showed anabsorption peak in the infrared spectrum at 2200 cm⁻¹, consistent with asulfonyl isocyanate.

EXAMPLE 2b N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide

To a suspension of 1.2 g of 2-amino-4,6-dimethylpyrimidine in 25 ml ofacetonitrile was added 2.6 g of 1,1'-biphenyl-2-sulfonyl isocyanate withstirring at ambient temperature. After stirring for 2 hours, the mixturewas filtered and the filtrate concentrated in vacuum. The residue thusobtained, after trituration with chlorobutane, melted at 78° with gasevolution. It showed peaks in the nuclear magnetic resonance spectrum(60 MHz) at δ 2.2, (singlet, CH₃); δ 6.56, (singlet, CH of pyrimidine)and at δ 6.8-7.9, (multiplet, phenyl hydrogens) in a ratio of 6:1:9,consistent with the desired structure.

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE XXXIII                                                    ______________________________________                                                    Active*                                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                              Emulsions, Solu-                                                              tions (including                                                              Emulsifiable                                                                  Concentrates   3-50     40-95     0-15                                        Aqueous Suspensions                                                                         10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and                                                                  Pellets       0.1-95      5-99.9  0-15                                        High-Strength                                                                 Compositions  90-99      0-10     0-2                                         ______________________________________                                         *Active ingredient plus at least one of a surfactant or a diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide", 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 1, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 5,line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 3

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,2'-Dichloro-N--[(4-methoxy-6-methyl-1,3,5-triazin-                          2-yl)aminocarbonyl] [1,1'-biphenyl]-2-                                        sulfonamide                80%                                                sodium alkylnaphthalenesulfonate                                                                         2%                                                 sodium ligninsulfonate     2%                                                 synthetic amorphous silica 3%                                                 kaolinite                  13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns and then reblended.

EXAMPLE 4

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)amino-                                       carbonyl] [1,1'-biphenyl]-2-                                                  sulfonamide              50%                                                  sodium akylnaphthalenesulfonate                                                                        2%                                                   low viscosity methyl cellulose                                                                         2%                                                   diatomaceous earth       46%                                                  ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles of active essentially all below 10 microns indiameter. The product is reblended before packaging.

EXAMPLE 5

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 4                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 6

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N--[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]                                [1,1'-biphenyl]-2-                                                            sulfonamide                25%                                                anhydrous sodium sulfate   10%                                                crude calcium ligninsulfonate                                                                             5%                                                sodium alkylnaphthalenesulfonate                                                                          1%                                                calcium/magnesium bentonite                                                                              59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 7

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        3,2'-Dichloro-N--[(4-methoxy-6-methyl-1,3,5-triazin-                          2-yl)aminocarbonyl] [1,1'-biphenyl]-2-                                        sulfonamide                  25%                                              polyoxyethylene sorbitol hexaoleate                                                                         5%                                              highly aliphatic hydrocarbon oil                                                                           70%                                              ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 8

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4-methoxy-6-methylpyridin-2-yl)                                          aminocarbonyl][1,1'-biphenyl]-                                                2-sulfonamide          20%                                                    sodium alkylnaphthalenesulfonate                                                                     4%                                                     sodium ligninsulfonate 4%                                                     low viscosity methyl cellulose                                                                       3%                                                     attapulgite            69%                                                    ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 9

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        N--[(4,6-dimethyl-1,3,5-triazin-                                              2-yl)aminocarbonyl][1,1'-                                                     biphenyl]-2-sulfonamide                                                                              40.0%                                                  polyacrylic acid thickener                                                                           0.3%                                                   dodecylphenol polyethylene glycol                                             ether                  0.5%                                                   disodium phosphate       1%                                                   monosodium phosphate   0.5%                                                   polyvinyl alcohol      1.0%                                                   Water                  56.7%                                                  ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 10

    ______________________________________                                        Low-Strength Granule                                                          ______________________________________                                        N--[(4,6-dimethoxy-1,3,5-triazin-                                             2-yl)aminocarbonyl][1,1'-                                                     biphenyl]-2-sulfonamide                                                                             0.1%                                                    attapulgite granules 99.9%                                                    (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 11

    ______________________________________                                        Granule                                                                       ______________________________________                                        3,2'-Dichloro-N--[(4-methoxy-6-methyl-1,3,5-triazin-                          2-yl)aminocarbonyl] [1,1'-biphenyl]-2-                                        sulfonamide                   80%                                             wetting agent                 1%                                              crude ligninsulfonate salt (containing                                        5-20% of the natural sugars)  10%                                             attapulgite clay              9%                                              ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water constant is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 12

    ______________________________________                                        High-Strength Concentrate                                                     ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)-                                            aminocarbonyl] [1,1'-biphenyl]-                                               2-sulfonamide             99%                                                 silica aerogel            0.5%                                                synthetic amorphous silica                                                                              0.5%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 13

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,2'-Dichloro-N--[(4-methoxy-6-methyl-1,3,5-triazin-                          2-yl)aminocarbonyl] [1,1'-biphenyl]-2-                                        sulfonamide                   90%                                             dioctyl sodium sulfosuccinate 0.1%                                            synthetic fine silica         9.9%                                            ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 14

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N--[(4-methoxy-6-methyl-1,3,5-triazin-                                        2-yl)aminocarbonyl] [1,1'-biphenyl]-                                          2-sulfonamide              40%                                                sodium ligninsulfonate     20%                                                montmorillonite clay       40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 15

    ______________________________________                                        Dust                                                                          ______________________________________                                        N--[(4,6-dimethylpyrimidin-2-yl)-                                             aminocarbonyl][1,1'-biphenyl]-                                                2-sulfonamide         10%                                                     attapulgite           10%                                                     pyrophllite           80%                                                     ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophllite until homogeneous.

EXAMPLE 16

    ______________________________________                                        Solution                                                                      ______________________________________                                        N--[(4,6-dimethoxypyrimidin-2-yl)-                                            aminocarbonyl][1,1'-biphenyl]-                                                2-sulfonamide, sodium salt                                                                            5%                                                    water                  95%                                                    ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

UTILITY

The compounds of the present invention are active herbicides. They haveutility for broad-spectrum pre- and/or post-emergence weed control inareas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,oil well sites, drive-in theaters, around billboards, highway andrailroad structures. By proper selection of rate and time ofapplication, compounds of this invention may be used to modify plantgrowth beneficially, and also selectively control weeds in crops such asrice and wheat.

The precise amount of the compound of Formula I to be used in any givensituation will vary according to the particular end result desired, theamount of foliage present, the weeds to be controlled, the soil type,the formulation and mode of application, weather conditions, etc. Sinceso many variables play a role, it is not possible to state a rate ofapplication suitable for all situations. Broadly speaking, the compoundsof this invention are used at levels of about 0.01 to 20 kg/ha with apreferred range of 0.1 to 10 kg/ha. In general, the higher rates ofapplication from within this range will be selected for adverseconditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and areparticularly useful in combination with3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines such as2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine); theuracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil);N-(phosponomethyl)glycine (glyphosate);3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione(hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamide);2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds);4-chloro-2-butynyl 3-chlorophenylcarbamate (barban);S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate);S-(2,3,3-trichloroallyl)diisopropylthiocarbamate (triallate);1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquatmethyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate(diclofop methyl);4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)one (metribuzin);3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron);3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon);α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin);1,1'-dimethyl-4,4'-bipyridinium ion (paraquat); monosodiummethanearsonate (MSMA); 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide(alachlor); 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea (fluometuron);N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (butachlor);4-(2,4-dichlorophenxoy)-2-methoxy-1-nitrobenzene (chlormethoxynil); andS-[(4-chlorophenyl)methyl]diethylcarbamothioate (thiobencarb).

The activity of these compounds was discovered in greenhouse tests. Thetests are described and the data resulting from them are shown below.

Test Procedure A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory(Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice,wheat and nutsedge tubers (Cyperus rotundus) were planted in a growthmedium and treated pre-emergence with a nonphytotoxic solvent solutionof the compounds of Table IV. At the same time, cotton having fiveleaves (including cotyledonary ones), bush beans with the thirdtrifoliate leaf expanding, crabgrass with two leaves, barnyardgrass withtwo leaves, wild oats with two leaves, cassia with three leaves(including cotyledonary ones), morningglory with four leaves (includingthe cotyledonary ones), cocklebur with four leaves (including thecotyledonary ones), sorghum with four leaves, corn with four leaves,soybean with two cotyledondary leaves, rice with three leaves, wheatwith one leaf, and nutsedge with three-five leaves were sprayed with anonphytotoxic solvent solution of the compounds of Table IV. Othercontainers of the above mentioned weeds and crops were treated pre- orpost-emergence with the same phytotoxic solvent so as to provide asolvent control. A set of untreated control plants was also included forcomparison. Pre-emergence and post-emergence treated plants and controlswere maintained in a greenhouse for sixteen days, then all treatedplants were compared with their respective controls and rated visuallyfor response to treatment.

The following rating system was used:

0=no effect

10=maximum effect

C=chlorosis or necrosis

E=emergence inhibition

G=growth retardation

H=formative effects

6Y=abscised flowers or buds.

                                      TABLE A                                     __________________________________________________________________________                 ##STR1160##                                                                                        ##STR1161##                                 kg/ha       0.1                  0.4       2                                  __________________________________________________________________________    POST-EMERGENCE                                                                BUSHBEAN    9C                   3C,3H     3C,7G,6Y                           COTTON      6C,9G                2C,2H,6G  3C,4H,9G                           MORNINGGLORY                                                                              10C                  4C,9G     3C,9G                              COCKLEBUR   4C,9G                2C,3H,8G  3C,9G                              CASSIA      3C,5G                2C,7G     2C,6G                              NUTSEDGE    5C,9G                9G        9G                                 CRABGRASS   2C,6G                5G        5G                                 BARNYARDGRASS                                                                             5C,8G                3C,9H     3C,9H                              WILD OATS   2C,8G                1C,2G     2C,9H                              WHEAT       2C,8G                2H,6G     2C,8G                              CORN        9C                   2C,8G     2C,9H                              SOYBEAN     9C                   2C,8H     2C,3H,9G                           RICE        5G                   --        --                                 SORGHUM     3C,9G                2C,8H     1C,9H                              PRE-EMERGENCE                                                                 MORNINGGLORY                                                                              9G                   9G        9G                                 COCKLEBUR   9H                   --        9G                                 CASSIA      1C                   9G        9G                                 NUTSEDGE    10E                  9G        10E                                CRABGRASS   3G                   4G        9H                                 BARNYARDGRASS                                                                             9H                   2C,9H     9H                                 WILD OATS   6G                   8G        8G                                 WHEAT       7G                   7G        8G                                 CORN        1C,9G                9H        9G                                 SOYBEAN     9H                   1C,6H     9H                                 RICE        5G                   9H        9H                                 SORGHUM     1C,9H                2C,9H     5C,9G                              __________________________________________________________________________

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus),morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti) and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugar beets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B. Note that certain compounds are useful as pre-emergencetreatments for weed control in crops.

                                      TABLE B                                     __________________________________________________________________________    PRE-EMERGENCE ON FALLSINGTON SILT LOAM SOIL                                            ##STR1162##                                                                                       ##STR1163##                                      Rate kg/ha                                                                            0.06      0.25      0.06       0.25                                   __________________________________________________________________________    Crabgrass                                                                             0         0         0          7C,8G                                  Barnyardgrass                                                                         2G        3C,4G     3C,5G      9C,9G                                  Sorghum 2G        3H,6G     9C,9G      9C,9G                                  Wild Oats                                                                             0         0         4G         4C,6G                                  Johnsongrass                                                                          0         2G        3G,6G      8C,9G                                  Dallisgrass                                                                           0         3G        5G         8G                                     Giant foxtail                                                                         2C,3G     3G        5H,7G      9C,9G                                  Ky. bluegrass                                                                         6C,6G     4C,6G     --         --                                     Cheatgrass                                                                            3C        3G        6G         10C                                    Sugarbeets                                                                            0         3G        3C,7G      8C,9G                                  Corn    0         2C,3G     4G         9C,9G                                  Mustard 9C,9G     3C,8G     8C,8G      9C,9G                                  Cocklebur                                                                             0         0         5H,6G      3H,6G                                  Pigweed --        --        0          5C,6G                                  Nutsedge                                                                              0         5G        7G         9G                                     Cotton  0         3G        2G         5G                                     Morningglory                                                                          2G        3G        8G         8G                                     Cassia  0         0         0          2G                                     Teaweed 0         5G        3C,5G      5G                                     Velvetleaf                                                                            4G        3H,4G     3H,5G      3H,5G                                  Jimsonweed                                                                            0         3C,5G     4G         3C,4G                                  Soybean 0         4G        5H,5G      5H,6G                                  Rice    2C,3G     2C,5G     5G         7G                                     Wheat   0         2G        3G         6G                                     __________________________________________________________________________

Test C

Twenty-five cm diameter pots filled with Fallsington silt loam wereplanted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum,velvetleaf, (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia(Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Daturastramonium), cocklebur (Xanthium pennsylvanicum), crabgrass (Digitariaspp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua).Approximately 21/2 weeks after planting, the young plants and the soilaround them were sprayed overall with the test chemicals dissolved in anon-phytotoxic solvent. Fourteen days after treatment, all species werecompared to untreated controls and visually rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C. Several of the compounds tested by thisprocedure are useful for the post-emergence control of weeds in crops.

                  TABLE C                                                         ______________________________________                                         ##STR1164##                                                                  Rate kg/ha       0.06        0.25                                             ______________________________________                                        Soybeans         2C,6G       3C,8G                                            Velvetleaf       1C,5G       2C,8G                                            Sesbania         1C,6G       3C,8G                                            Cassia           2G          1C,3G                                            Cotton           2C,3G       3C,7G                                            Morningglory     3C,9G       6C,9G                                            Alfalfa          0           --                                               Jimsonweed       --          --                                               Cocklebur        2C,5G       3C,5G                                            Corn             2G          2G                                               Crabgrass        1C,2G       1C,2G                                            Rice             2G          3G                                               Nutsedge         7G          8G                                               Barnyardgrass    1C,5G       2C,6G                                            Wheat            0           2G                                               Giant Foxtail    5G          1C,5G                                            Wild Oats        1G          2G                                               Sorghum          1G          3G                                               ______________________________________                                    

Test D

Purple nutsedge (Cyperus rotundus) tubers were planted in 2 cm deep inFallsington silt loam soil contained in 10 cm diameter plastic pots.Five tubers were planted in each pot. Compounds of this invention weredissolved in a non-phytotoxic diluent and sprayed at 560 l/ha in fourmethods of application: soil surface, tuber/soil, soil incorporated andpost-emergence. The soil surface spray consisted of spraying thecompound on the surface of the firmed covering soil. The tuber/soilspray consisted of spraying the compound on exposed tubers andsubtending soil before adding the untreated covering soil. Soilincorporated treatment consisted in mixing the compound with thecovering soil before using it to cover the tubers. The post-emergencetreatment was sprayed on nutsedge foliage and the surrounding soilsurface when nutsedge had emerged and grown to a height of about 12 cm.Pots receiving the post-emergence treatments were placed directly in thegreenhouse. Pots receiving the other treatments were misted with about0.3 cm water before being transferred to the greenhouse. Responseratings assessed after four weeks are recorded in Table D based on thesame rating system as described in the procedure for Test A.

                  TABLE D                                                         ______________________________________                                         ##STR1165##                                                                           Pre     Pre         Pre    Post                                      Rate,    surface tuber & soil                                                                              soil inc.                                                                            foliar                                    kg/ha    spray   spray       2.5 cm spray                                     ______________________________________                                        0.125    0       5G          7G     3G                                        0.5      0       8E,9G       9G     5G                                        ______________________________________                                    

What is claimed is:
 1. A compound selected from ##STR1166## n is 0 or 1;R₁ is H, F, Cl, Br, NO₂, CF₃, C₁ -C₄ alkyl, OCF₃ or C₁ -C₄ alkoxy;R₂ andR₃ are selected independently from H and CH₃ ; R₄ is H, C₁ -C₃ alkyl, F,Cl, Br, CF₃, OCF₃ or C₁ -C₃ alkoxy; R₅ is CH₃, Cl, Br or H; A is##STR1167## X is H, CH₃, OCH₃, OCH₂ CH₃, OCH₂ CF₃, CH₂ OCH₃ or Cl; Y isCH₃, OCH₃ or OCH₂ CH₃ ; Z is N, and Q is CH₂ or O;provided that thetotal number of carbons in R is less than or equal to nine.
 2. Acompound of claim 1 in which n is
 0. 3. A compound of claim 2 in whichAis ##STR1168## X is CH₃, OCH₃, OCH₂ CH₃ or CH₂ OCH₃ ; Y is CH₃ or OCH₃ ;and Z is N.
 4. A compound of claim 3 in which R₅ is H, and R₄ is H orCl.
 5. A compound of claim 4 in which R₁ is H or Cl.
 6. A compound ofclaim 1 which is3,2'-dichloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl][1,1'-biphenyl]-sulfonamide.7. A compound of claim 1 which isN-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide.8. A compound of claim 1 which isN-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide.9. A compound of claim 1 which isN-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide.10. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid or liquid diluent.11. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.12. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid or liquid diluent.13. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid or liquid diluent.14. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid or liquid diluent.15. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 6and at least one of the following: surfactant, solid or liquid diluent.16. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 7and at least one of the following: surfactant, solid or liquid diluent.17. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 11and at least one of the following: surfactant, solid or liquid diluent.18. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 12and at least one of the following: surfactant, solid or liquid diluent.19. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 20. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 21. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 22. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 23. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 24. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim6.
 25. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 7. 26. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 8. 27. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim9.